Aim for Heaven and Wind up in Hell
by DontKnowMyName
Summary: Sam understands the horrors associate with Hell. He knows the fear that is played against the souls rotting within the fiery depths. Slightly AU
1. Chapter 1

Title: Aim for Heaven and Wind up in Hell

Author: DontKnowMyName

Rating: PG-13

Disclaimer: Characters aren't mine. Title belongs to Bad Company's song "Crazy Circles."

Warnings/spoilers: AHBL and 4x10

A/N: I actually did the math for this story (too bad all math problems can't relate to Supernatural)**. This story assumes Sam was dead for two days before Dean made his deal and if so than I'm 99% sure the math is correct.**

Summary: Sam understands the horrors associate with Hell. He knows the fear that is played against the souls rotting within the fiery depths. (Slightly AU)

_______________________

This makes two roadside confessional breakdowns for Dean, not that Sam is keeping score or anything. Dean never expected him to have an answer to his problems on either occasion so Sam never offers any ideas. He barely speaks. The first time, however, Sam actually saw the tears, he could even feel them. He had a reason to share in some of Dean's grief then, but this time he knows it is all Dean's. He can't possibly share the sorrow his brother is feeling.

To say Sam doesn't understand would be completely wrong though. He understands, probably better than anyone else on the entire earth, even Castiel. Sam understands the horrors associate with Hell. He knows the fear that is played against the souls rotting within the fiery depths. He can't tell that to Dean though. All he can do is listen this time.

He watches Dean from behind but makes no effort to see his brother's face. Watching Dean cry will only add humiliation to the emotional baggage, if Dean isn't already feeling it. Sam settles on simply being there, offering Dean something Sam's only ever been given by his big brother: understanding, faith and of course love.

It takes every ounce of Sam's will power not to wrap his long arms around Dean's shoulders and hug him close. He wants to tell Dean everything's okay, that he wishes he could take the pain away and fix Dean all together, but he knows none of that will help. Dean was gone for what apparently felt like forty years, forty years of pain and fear, forty years while Sam lived in the daylight. Nothing Sam could think of would ever make that okay, but he will never give up on his attempts to ease the weight on Dean's mind.

"Sam?" Dean finally asks, apparently composing himself while Sam was lost in his own thoughts. "Ready to get moving?"

He watches as Dean tosses the empty beer bottle into the shrubs to Sam's left, listening as the glass shatters. The sharp pop of the bottle cracking still manages to startle him and his eyes quickly find Dean's in the early afternoon sun. Dean looks completely broken and Sam's mind wanders back to the discarded bottle. There was no fix. No glue could put together the millions of pieces scattered about the bushes; assuming all pieces could even be found. Dean can't be fixed either. Sam can't magically put his brother's soul back together again. There were too many fractured pieces and some were lost forever.

"Yea," He whispers as he hops off the Impala's hood and gives his bottle a long glance before throwing it into the shrubs as well. "Let's go."

The more Sam thinks about what is happening, the more he realizes that there is absolutely nothing he can do. How on earth could he fix Dean? That's like asking a blind doctor to perform surgery. One brother, tainted and broken, can't fix another.

He can accompany Dean on his road of misery, but that just doesn't feel right. While he doesn't want Dean to feel alone he also doesn't want to smother Dean or encroach on his private suffrage. All thoughts leave him though as Dean pulls the car back onto the road and they are once again on the open highway, the tension in the air much thinner now.

That night Sam wakes in a cold sweat, cheeks sticky with tears and his throat sore. The mattress dips on his right and he feels a gentle hand rest on top of his chest, smoothing the wrinkles out of his shirt. His eyes remain shut but he knows the presence and familiar touch, which allows his racing heartbeat to slow.

"You were dreaming, Sam," Dean's whisper is soothing and Sam eases back into the pillow.

For a few seconds Dean doesn't say anything, and Sam thinks he's going to be allowed to fall back to sleep, but of course not. Dean stands for what feels like a second before he returns with a cool rag that he gently lies across Sam's forehead.

"What was it about?"

"Nothing."

"Nothing?" Sam can feel Dean shake his head. "Nothing doesn't cause you to scream out in the middle of the night, quite possibly waking the whole motel."

"I'm sorry," The rag moves slowly from his forehead and wipes along his cheeks. "I'm okay now."

He attempts to push Dean away but instead ends up grabbing onto his brother's wrist. The second his hand latches onto Dean the emotions come flying back to him. Everything from the dream and everything from the day's events flood his mind.

Springing up into a sitting position his hands move up Dean's arms to grasp shoulders, holding tight as if his life depended, and right now it surely feels like it did. Dean stares at him curiously, eyes searching his in the poorly lit room. He shakes his head and the tears welling up in eyes roll down his cheeks once more as he pulls Dean toward him, wrapping his arms across his brother's back.

Part of him argues that Dean will be angry and that he must let go, but right now Sam isn't thinking correctly. All that's running through his mind is how much he needs Dean. He can feel the fear wash away as Dean's heartbeat pulses in time with his own and Sam tightens his hold, afraid if he lets go it will all come back.

"Sammy," Dean forces them to break apart, but continues to hold onto Sam's shoulders as Sam tries to pull Dean back to him. "It's okay. I'm right here."

"Please don't leave."

The words come out without so much as a thought and the weakness of his own voice scares him. Obviously they have the same effect on Dean because a second later Sam can feel Dean pull him back and strong arms tightly wrap around Sam's shoulders. He lets his head fall against Dean's shoulder, tears continuing to fall at a steadier pace.

"That's what this is about?"

"I couldn't save you."

"You tried, Sammy, I know you tried." Dean squeezes tighter, emphasizing each word.

"You suffered so much longer than I did."

"Sam," He can tell Dean is getting aggravated. "It's not a contest."

"I was there, Dean," He wants to stop. He doesn't want to confess, to tell Dean he's been keeping another secret. "I know what it's like."

"What?" Dean's eyes are large with confusion as well as concern.

"When I died," Sam lowers his head, unable to look at Dean any longer. "I went to hell, it was different, but I was there. I saw it. I felt it. I was there for 2 days, Dean, 4 months in hell."

"You're lying."

"No."

Dean's hold on Sam breaks at that and Sam curls into himself to compensate for the missing comfort. He rocks himself back and forth, keeping his head down and rests it atop his knees as Dean paces in front of the bed nervously. This is exactly why Sam never told Dean.

When Dean ended up in Hell it was for a noble reason, no matter how stupid, it was at least not a result of his character or ties. Well, now that Sam thinks about it, technically it was because of Dean's family ties but it wasn't as direct as Sam's. No, Sam had ended up there because of his blood. Not the blood he shared with Dean but the blood fed to him as a baby.

Hell had claimed his soul before Sam could even speak and that made Sam a VIP in the pit. His time spent in damnation was different than Dean's but similar as well. Sam was never placed on a rack but he was offered a deal much like the one Alastair offered his brother. That's what makes Sam feel even worse and Sam can't even hear himself think anymore as his cries become louder.

"Sammy," Those calming hands were back but this time they felt like fire.

Sam tried to pull away put Dean's left arm wraps around him, pulling Sam's entire body against his chest as his right arm lowers Sam's head to his shoulder. Dean's chin rests atop Sam's head as his hand gently brushes through Sam's long hair. It only takes a few seconds before Sam's breathing returns to normal and his sobs turned into hiccups.

"I didn't even last a week," He turns his head further into Dean's chest even as his mind tells him not to. "I gave in after day three, Dean."

All this time he wanted Dean to talk about hell, he told himself it was best if Dean opened up and shared his horrific experience. Turns out he needed it just as much, if not more than Dean did. He hates himself for making his brother deal with his emotions when Dean had plenty of his own to work through.

Dean doesn't say anything though, and both arms tightened around Sam's body, hands rubbing gently up the side of Sam's own arm. After a few minutes Sam realizes Dean's giving him the opportunity to continue. He wants to turn away and deal with it on his own, to suck it up and be tough, but it's no secret he handles grief and any other emotion much different than Dean.

"They never tortured me, at least not physically, but they showed me things. They showed me everyone I loved…" He takes a deep breath, releasing his hold on his knees and lowering his feet to the floor. "Everyone I ever cared about. They showed me what would happen to you all if I didn't give in, if I didn't become the leader I was born to be."

Again Dean tightens his arms around Sam and this time Sam brought his own arms around his brother, bringing them both even closer. Sam continues to let his tears fall as he rests contently against Dean, listening to his brother's heart. His body feels completely drained when his tears finally started to slow and he feels his eyes begin to drift close just as Deans decides to speak.

"I would have done the same."

"You didn't," Even tired, Sam can't deny the fact that Dean hadn't given in like him, that Dean actually felt the unbearable pain that Sam had inflicted on other souls, yet Dean stayed strong. He wasn't weak like Sam. He wasn't evil like Sam.

"No I didn't," Dean corrects himself as his right hand moves back up to Sam's hair. "But it was different for me, Sam."

"It was worse."

"Sammy, I've beaten people up for looking at you funny. I've shot humans, though they were possessed, for laying their hands on you. Don't you think I would have given in the second they brought you into the story?"

It takes a bit for Sam to comprehend everything Dean said but he silently thanks his brother for not mentioning that his trip to hell was because of Sam in the first place. Even though it's clearly on Sam's mind, hearing Dean say it would probably have sent him over the edge. The words Dean chooses wisely are exactly what Sam needs to hear, yet he still remains slightly confused.

He doesn't understand why they used Dean and his loved ones against him, yet didn't use that same leverage on Dean. Anyone who has ever wanted to get to Dean, and had known Dean well enough to push the right button, has gone right after Sam. There was no denying that Sam was Dean's Achilles heel.

"They wanted you to give in, Sammy," Of course he should have known Dean could read his mind, just another big brother trait Hell hadn't managed to steal. "I don't care what you believe, but you are a good person and even if Hell seemed to get their hands on you, they still knew you weren't their material."

"What?" He is much too tired for Dean's logic apparently.

"Your connection to the demon may have put you there, Sam, but you weren't one of them so therefore they had to make you one."

"But why, why didn't they hurt me like you?"

"I'm already and asshole," Dean snickers and Sam can't help but smile himself. "They hurt you by making you something you're not."

"And what's that?"

"Weak and cruel."

"But I am weak, Dean, don't you get it?" He shakes his head and pulls back from his brother, staring right into Dean's eyes. "I couldn't last."

"Damn it Sam," This time there was anger in Dean's voice as he rubs against his temples in obvious annoyance. "The only god damn reason I lasted so long is because they reminded me you were safe. They knew I would hold on much longer knowing you were safe. Had they wanted to break me faster, then they would have pulled the same shit they did to you."

"I'm sorry," For once Sam has nothing else to say.

"You ought to be."

Sam's eyes widen as he looks back up at Dean, searching him for the forgiveness he knows he doesn't deserve but desperately seeks. The smile he finds only freaks him out more before he feels Dean's arms wrap around him again, pulling him close. Sam's reluctant to return the gesture this time until Dean's arms begin their calming movement up and down his back.

"You ought to be sorry that you didn't tell me sooner," Dean whispers into Sam's ear, squeezing his arms tighter around his little brother. "Damn you for being so macho and unable to share your feelings."

"I learned from the best." Sam laughs and squeezes his arms around Dean as well before pulling back and breaking their contact. "Hey, Dean?"

"Yeah?"

"You think you could convince Castiel to put a good word in for me?" A sheepish smile spreads across Sam's lips as Dean throws his head back and laughes.

"I'll see what I can do."

**-DontKnowMyName-**

_Please let me know what you guys think._

_I'm contemplating doing another chapter that would focus on Dean's reaction but your reviews will help me decide._

_Hope you all had a lovely holiday!  
_


	2. Chapter 2

Title: Aim for Heaven and Wind up in Hell

Rating: PG-13

Disclaimer: Characters aren't mine. Title belongs to Bad Company's song "Crazy Circles."

Warnings/spoilers: AHBL and 4x10

A/N: I actually did the math for this story (too bad all math problems can't relate to Supernatural). **This story assumes Sam was dead for two days before Dean made his deal and if so than I'm 99% sure the math is correct.**

Summary: Sam understands the horrors associate with Hell. He knows the fear that is played against the souls rotting within the fiery depths. (Slightly AU)

_______________________

There are five cracks in the ceiling, six spots on the wall where the paint is chipping, one oddly shaped hole to the left of the bathroom door and the table leans slightly to the right. When he starts to count the numerous stains on the carpet, Dean finally realizes he needs to either get out or go to sleep. Getting some fresh air definitely seems more appealing.

The old fashion alarm clock between the beds reads midnight, meaning it's only been about twenty minutes since Sam's fallen asleep but it feels like it's been hours. Dean's eyes drift to his brother's sleeping form; his head turned toward Dean, hair covering his eyes and making him look no older than eight.

There's absolutely no way Dean could sleep now. On top of his own nightmares of hell he knows his mind will plague him with thoughts of Sam's as well.

How could someone like Sam end up somewhere as awful as Hell and how could Dean possibly believe in God if nothing had been done to save his brother.

He wants to be pissed at Sam for giving him more to think about and pissed at God for letting it happen, but he knows the only person he's angry at is himself. His life has always revolved around two things, one always falling above the other, but somehow he's let that slip.

Since he's been back from hell he's done so much to fix up the Impala, slightly frustrated that Sam hadn't paid his baby much attention. And right there is where he should have realized things just weren't right.

He's been in hell for four months, left his brother all alone, and yet he seriously expected Sam to take excellent care of a car? He should have seen Sam had barely taken care of himself let alone the Impala, but he's not even sure he's given Sam much though since he's been back. What the hell kind of brother does that make him?

So he has a few tormenting memories flashing in his head every time he closes his eye. Apparently Sam's had to deal with his memories for a year, and then on top of that had the knowledge that Dean would be in that same place.

Dean probably should have seen it coming, or at least had some kind of doubt about his brother's afterlife. Sam's real life had been hell, why not send the kid to the pit and make him suffer more.

Back than Dean hadn't known everything he does now, which actually made it all ten times worse. His doubts about God still pull at the back of his head, especially after recent events.

Angels are apparently real though and if these angels have the power to pull Dean out of Hell, then what the heck were they doing when Sam was there? If anyone deserved saving it was Sam.

Dean stands quickly, unable to sit in the room any longer as his thoughts suffocate him. He grabs his jacket from the chair and heads for the door, sparing Sam one last look before exiting the room into the cool night air.

He pulls the keys from his pocket as he heads toward the trunk, wanting nothing more than to down the half empty bottle of whiskey he keeps there. That's become the only way he's willing to deal with his problems as of late, swallowing them in the numbness of alcohol.

The wind picks up suddenly, causing the hairs on Dean's neck to stand in alertness. He turns around slowly, knowing exactly what, or who, he will find standing in the darkness.

"You're about the last person I want to see right now."

Castiel sighs and lowers his head for a second before bringing his eyes back up to meet Dean's. Had the situation been different, Dean probably would have laughed at the idea that an angel could look or feel guilty.

"I came to set things straight," Dean shakes his head and turns back to the car, finally opening the trunk and pulling out the whiskey. "Sam wasn't of interest until you went to hell."

"That just lovely," He twists the cap free so aggressively that he thinks for a second the bottle might shatter, and wouldn't that be a funny bit of irony. "So my brother rots in hell and you think nothing of it until I'm in the same situation a year later? What makes Sam any less important than me?"

"One life is no more important than another, Dean Winchester."

"Then why the fuck didn't you save him?" Dean's voice rises and he instinctively moves forward toward the angel. "You could have saved him! You could have stopped his suffering, his doubts about his humanity, his doubts in me and God! He was a good kid."

"Are you saying he is no longer a good man?"

"No!" His anger flies to a new level and he can't stop himself from throwing his bottle across the parking lot. "Do not use my words against me! You and your buddies decide I'm worth saving only to tell me I have to stop my brother from being evil? You put these doubts in my head! You turned me into this horrible brother."

Finally Dean turns away with a sigh, feeling even worse. He hasn't said the words out loud yet but that seems to put things into perspective.

Dean's doubted Sam ever since Castiel showed him what happened to his brother. He's been so caught up on Sam possibly not being Sam that he forgot about being Dean.

He's noticed how far he and Sam have started drifting apart but he has done nothing to stop it from happening. Anger, fear and suspicion have become the only three emotions ruling his life.

The last time he can remember showing any sign that he cared about Sam was when they finally reunited after Hell tore them apart. All he's done since then is fight with Sam about powers and Ruby. He's thrown all his doubt straight in Sam's face yet Sam stuck by his side.

"You still care about your brother." Castiel's deep voice pulls him from his thoughts.

"Bang up job I did of showing it." He confesses with a small smirk.

"You were willing to give up Anna to save him."

"I actually thought about it though," Dean closes his eyes and runs his hand through his hair, letting it rest against the back of his neck. "I thought about it, Cas. It wasn't a quick decision like it usually is. What the hell is wrong with me?"

"You're scared," The angel takes a step forward and gently places a hand on Dean's shoulder. "I did not help you much but I am here to change that. You're brother needs you, Dean. He is still the little brother you remember, but only when his big brother is there."

"Why did you tell me I had to stop him," His voice remains soft even though there is still anger in his words. "You made me think he was a monster. I can't believe I let myself think that."

"Sam's powers are his connection to Hell."

"Excuse me?"

"As long as your brother continues to use his powers, Hell will continue to hold his soul."

"He wasn't using his powers the first time."

"Azazel was still alive. The blood tie was still there."

"Even if Sam stops, the blood would still be in his veins."

"The blood is similar to a muscle in Sam's case. The more Sam uses his powers the stronger the connection becomes."

"Okay so by not using them he will still carry the blood but he won't have a connection to hell?"

"Correct," Castiel smiles slightly. "Sam's powers allow Hell to keep track of him and if Sam uses them they will have grounds to claim his soul since the powers are a gift from a demon."

"Sam doesn't know this?"

"No," The angel's smile falls instantly and he looks away from Dean. "The demon your brother is working with does though, which is why their relationship must end."

Even if Dean has suspected it all along, hearing it confirmed does not make him feel any better, especially after he practically thanked the bitch for helping Sam. Yeah she may have kept Sam from getting himself killed but at what cost?

"Why didn't you guys stop him?"

"We tried," Their eyes meet again, conveying the truth in the angel's words. "We couldn't reach Sam. By using his Demon powers he was blocking us. We also could not risk appearing to him with ruby around. Sam most likely would not have listened to us anyways. He had started losing his faith shortly after you were gone."

"So is this why I was resurrected?"

"One of the reasons, yes." The angel gestures toward the brother's motel room. "You're brother is too vulnerable without you around, you were the only person who could cease his activities or so we had hoped. You are also a strong asset to our defense. We needed you to keep the evil at bay."

"Sam wasn't doing enough of that?"

"Sam was helping but also destroying himself. He needed to be saved as did you. The two of you, together, are what will help us win this war."

"You saved me so that I could save Sam?"

"Yes."

Dean smiles, "I can do that."

"We know," Castiel smiles as well, placing his hand on Dean's shoulder once more. "You are a good brother, Dean. I never meant to make you doubt yourself or Sam, but if Sam does not stop, the only way to save his soul is for us to intervene and unfortunately that is not a pleasant ending either."

"Well it won't come to that." Dean stands straighter, feeling better about himself and the reason behind his redemption. "He's still my little brother, I can save him."

"That is what you're best at," The angel chuckles, enjoying the life that has been restored in Dean. "Sam is still Sam and with you around he will no longer need the comfort that Demon has been pretending to supply. Go to him, Dean, he needs you."

Castiel raises his hand slowly to touch Dean's forehead and Dean recognizes the gesture a second before his eyes snap open once more. He gasps slightly at the surprise of being back in the motel room, lying flat on the bed across from his brother's.

A murmur from beside him draws his attention and he turns his head to the side only to find Sam burying his head into the pillow. For all the nights Dean's woken up to Sam's nightmares, he wonders just how many he's missed.

It's been over a year since Sam's been in hell, he's confessed to remembering, and that most likely means he's had similar nightmares in the nights before Dean went to hell. He can only imagine the nightmares that plagued the kid while Dean wasn't here.

"Dean," The sound is so quiet that he almost misses.

Sam's head remains buried in the pillow but Dean can hear the mumbled words as he climbs out of his own bed and makes his way to Sam's. He takes a seat beside his brother and gently rests his hand on the back of Sam's head.

"Sammy," He whispers. "Wake up, buddy, it's just a dream."

"No, please," Sam turns his head from side to side frantically, face digging into the pillow further. "Dean!"

"Sammy!" In a flash, Sam jumps awake, almost knocking Dean backwards as he turns on to his back. "I'm right here."

"Hi," Sam smiles slightly, running his hand through his sweating locks, cheeks flushed with embarrassment.

"Hi," Dean lets himself smile as well, reaching his hand out to cup Sam's neck. "How you feeling?"

"Confused."

"You and me both, brother."

"Thanks," Sam's eyes drop to his hands, now folded in his lap. "You know, for being here."

"I'm sorry I've been such an ass lately, Sam," Dean's hand slips to Sam's chin, forcing their eyes to meet. "I should have seen that all of this affected you too, and I'm sorry I didn't."

"You were in hell, Dean."

"Yeah and apparently so were you. I know you understand that things are a little crazy for me right now and I appreciate that but it's no excuse for how I've been treating you."

"Well you have been a bit different."

"You think?"

"Yeah," Sam laughs softly. "You're a bit of a pansy lately."

"Real nice, Sam," He tries to feign anger but he ends up laughing himself. "I guess our roles reversed a little, huh?"

"I guess, but can we go back to normal now?" Dean laughs again, the look on Sam's face and the tone in his voice reminding Dean too much of the little boy Sam used to be.

"I think so. You're not a good me, anyways."

"I'm just not big brother material."

"Luckily, I am." He smiles and pats Sam on the shoulder as he stands up and moves back to his own bed. "It's the role I was born to play."

"Thank God."

"Yeah," Dean's smile falters a tad, contemplating the idea of telling Sam everything Castiel had told him. Sam's eyes start to fall close though, a smile spreading his lips, and Dean decides it's best to leave everything just the way it is. Things are back to normal, or as normal as they could get, and he would save Sam. That was one mission he would never fail. "Thank, God."

**-Dontknowmyname-**

_Thank you all for reading! I hope you enjoyed this chapter as much as the first._

_Please let me know what you thought, even if you didn't like it at all, I still would love to hear from you._

_I'm pretty sure this is where I'm ending it cause there really is no where else to go unless I started my own new supernatural season haha, but you never know with me._

_Thanks again!_


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